CN114113018B - Fluorescent detection method for measuring zinc ions by taking tetranitrophthalocyanine as reagent - Google Patents

Fluorescent detection method for measuring zinc ions by taking tetranitrophthalocyanine as reagent Download PDF

Info

Publication number
CN114113018B
CN114113018B CN202111437993.5A CN202111437993A CN114113018B CN 114113018 B CN114113018 B CN 114113018B CN 202111437993 A CN202111437993 A CN 202111437993A CN 114113018 B CN114113018 B CN 114113018B
Authority
CN
China
Prior art keywords
tetranitrophthalocyanine
fluorescence
zinc ions
zinc
solution
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Active
Application number
CN202111437993.5A
Other languages
Chinese (zh)
Other versions
CN114113018A (en
Inventor
李东辉
张艳
黄萍
邓雅斌
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Xiamen University
Original Assignee
Xiamen University
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Xiamen University filed Critical Xiamen University
Priority to CN202111437993.5A priority Critical patent/CN114113018B/en
Publication of CN114113018A publication Critical patent/CN114113018A/en
Application granted granted Critical
Publication of CN114113018B publication Critical patent/CN114113018B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
    • G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
    • G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
    • G01N21/64—Fluorescence; Phosphorescence
    • G01N21/6402—Atomic fluorescence; Laser induced fluorescence
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N1/00—Sampling; Preparing specimens for investigation
    • G01N1/28—Preparing specimens for investigation including physical details of (bio-)chemical methods covered elsewhere, e.g. G01N33/50, C12Q
    • G01N1/38—Diluting, dispersing or mixing samples

Landscapes

  • Health & Medical Sciences (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Analytical Chemistry (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Immunology (AREA)
  • Pathology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Optics & Photonics (AREA)
  • Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)

Abstract

A fluorescence detection method for measuring zinc ions by taking tetranitrophthalocyanine as a reagent relates to zinc ion measurement. 1) Adding an organic solvent as a reaction medium into a reaction vessel; 2) Adding the same volume of tetranitrophthalocyanine organic solution into each reaction container; 3) Sequentially adding zinc ion organic solution with increasing concentration; 4) Constant volume, mixing, preserving heat in water bath for a certain time, transferring into ice water, and cooling; 5) Taking out the solution, scanning the fluorescence spectrum of the reaction system, and measuring the relative fluorescence intensity at the fluorescence peak. The tetranitrophthalocyanine is used as a fluorescent probe to measure zinc ions with high sensitivity and high specificity, the detection sensitivity is high, the specificity is strong, and common metal ions are not interfered. The operation is simple and convenient, and visual observation can be realized. The interference of scattered light during measurement can be effectively avoided; since fluorescence emission of natural and artificial fluorescent substances is extremely small in the detection wavelength region, interference of background fluorescence can be avoided.

Description

Fluorescent detection method for measuring zinc ions by taking tetranitrophthalocyanine as reagent
Technical Field
The invention relates to zinc ion determination, belongs to the technical field of fluorescence analysis, and particularly relates to a fluorescence detection method for determining zinc ions by taking tetranitrophthalocyanine as a reagent.
Background
Zinc has wide application in production and life. In the pharmaceutical industry, zinc is prepared into medicaments such as zinc undecylenate, zinc citrate, zinc oxide, zinc gluconate, zinc sulfadiazine and the like, and is applied to the treatment of various diseases [ Chan, S.et al.Trans Oncology,2019,12 (5): 788-799; liu, J.L.et al, 2019,783:898-918; cankovic, M.et al 2018,26 (2): 125-132]. In industry, zinc can form more excellent alloys with other metals, such as zinc-copper-titanium alloys, which have been widely used in airports, exhibitions, churches, clubs, etc. buildings since the 70 th 20 th century because of their low cost, long service life, and low maintenance frequency [ Ji, S.Y.et al., materials and Corrosion-Werkstoffe Und Korrosion,2017,68 (4): 458-467)]. Because zinc has strong corrosion resistance, the zinc is often used as a corrosion-resistant coating material to protect other metal structures and is widely applied to ships, automobiles, buildings and the likeIndustry (e.g.) [8,9,10] . In addition, zinc has the characteristics of abundant material sources, low cost, good chemical stability and good environmental compatibility, and is used as a negative electrode material to be matched with manganese dioxide, prussian blue analogues, vanadium-based compounds and other positive electrode materials to form a battery with excellent performance (Chen, X.Y., et al, journal of Energy Chemistry,2019, 38:20-25). In the chemical field, zinc is also a very good catalyst for catalyzing the progress of the corresponding chemical reaction [ Alshakova, I.D., et al Synthesis-Stuttgart,2019,51 (17): 3305-3312)]。
Common analytical methods for zinc include liquid chromatography, infrared spectroscopy, inductively coupled plasma emission spectroscopy, potentiometry, atomic absorption spectroscopy, differential scanning calorimetry, and the like. The methods are complicated to operate by using large instruments. Therefore, the development of a simple, convenient, easy-to-operate, good in selectivity, sensitive and practical zinc ion analysis method has important practical significance.
Disclosure of Invention
The invention aims to provide a fluorescence detection method for measuring zinc ions by using tetranitrophthalocyanine as a reagent, which has the advantages of strong specificity, high sensitivity, high accuracy and good stability, and can effectively eliminate interference of background fluorescence and scattered light in an actual sample when the measurement wavelength is in a long wave region. Based on the reaction of tetranitrophthalocyanine and zinc ions, the reaction system emits red fluorescence to determine the zinc ions.
The method comprises the following specific steps:
1) Adding an organic solvent as a reaction medium into a reaction vessel;
2) Adding the same volume of tetranitrophthalocyanine organic solution into each reaction container;
3) Sequentially adding zinc ion organic solution with increasing concentration;
4) Constant volume, mixing, preserving heat in water bath for a certain time, transferring into ice water, and cooling;
5) Taking out the solution, scanning the fluorescence spectrum of the reaction system, and measuring the relative fluorescence intensity at the fluorescence peak.
In step 1), the number of the reaction vessels is not less than 3; the organic solvents used as the reaction medium include, but are not limited to, the following: methanol, N-dimethylformamide, absolute ethanol, tetrahydrofuran, triethylamine, piperidine, ethylene glycol methyl ether, ethanolamine, ethylene glycol, N-pentanol, N-heptanol, isoamyl alcohol, N-butanol, N-nonanol, N-hexanol, N-octanol, ethyl acetate, petroleum ether, acetonitrile, N-propanol, dimethyl sulfoxide, sulfolane, acetone, 1, 4-dioxane, tetramethyl ethylenediamine, triethylene tetramine, carbon tetrachloride, N-heptane, iodooctane, methylene chloride, chloroform, cyclohexane, benzene, nitrobenzene, acetylacetone, liquid paraffin, methyl methacrylate, oleyl alcohol, xylene, benzothiazole, quinoline, isopropylamine, butylamine, pyridine, and morphine.
In step 2), the tetranitrophthalocyanine has the formula C 32 H 14 N 12 O 8 ；
The structural formula is as follows:
the organic solvent used in the tetranitrophthalocyanine organic solution is selected from dimethylformamide, dimethyl sulfoxide, chloronaphthalene, quinoline, nitrobenzene and other organic solvents with higher solubility for tetranitrophthalocyanine; the tetranitrophthalocyanine solution has a final concentration of 1.0X10 -6 ～2.0×10 -5 A corresponding amount of tetranitrophthalocyanine solution in mol/L.
In the step 3), the solvent used in the zinc ion organic solution is selected from organic solvents with high solubility for zinc compounds, such as methanol, ethanol, propanol, acetone, acetonitrile, dimethylformamide, dimethyl sulfoxide, sulfolane and the like; the series concentration of the zinc ion organic solution falls within the corresponding linear range of the working curve, wherein the corresponding linear range of the working curve refers to the linear range of the working curve which corresponds to the determined concentration of the zinc ion by the concentration of the tetranitrophthalocyanine solution.
In the step 4), the time of the water bath heat preservation is not less than 60min.
In step 5), the relative fluorescence intensity at the measured fluorescence peak may be measured in a wavelength range of 660 to 760 nm.
The reaction according to the invention is carried out in an organic medium. In the organic medium, the fluorescence of tetranitrophthalocyanine with a central noncoordinating atom is very weak, i.e. the fluorescence background of the reaction system is very low. In the presence of zinc ions, tetranitrophthalocyanine and zinc ions undergo a coordination reaction to form zinc phthalocyanine. The reaction system emits red fluorescence under the excitation of ultraviolet light or light with the wavelength of more than 600nm, and the maximum emission wavelength is about 711nm. Therefore, a novel fluorescent detection method for measuring zinc ions with high specificity and high sensitivity by taking tetranitrophthalocyanine as a fluorescent probe is established. Compared with the prior art, the invention has a plurality of advantages, mainly comprising:
1) The fluorescence detection method for measuring zinc ions with high sensitivity and high specificity by taking tetranitrophthalocyanine as a fluorescent probe is not reported, and is an original invention.
2) The detection sensitivity is high. The detection limit of the zinc ion detection method established by the invention is as low as 3.0 multiplied by 10 - 8 mol/L, or 5.5X10 -9 g/mL, ppb level, is significantly better than most reported zinc ion detection methods.
3) The specificity is strong, and common metal ions have no interference.
4) The operation is simple and convenient, and visual observation can be realized. 5.0X10 -7 The mol/L zinc ion solution can show visible red fluorescence, which is very beneficial to on-site analysis.
5) The wavelength of the measurement is greater than 700nm and is located in the red (long wavelength) region of visible light. Because the scattered light is proportional to the fourth power of the wavelength, the interference of the scattered light during measurement can be effectively avoided; since fluorescence emission of natural and artificial fluorescent substances is extremely small in the detection wavelength region, interference of background fluorescence can be avoided.
Drawings
FIG. 1 shows the excitation spectrum and fluorescence spectrum of a reaction system in the absence of zinc ions.
FIG. 2 is a comparison of the fluorescent response of tetranitrophthalocyanine to zinc ions versus common metal ions.
FIG. 3 is the effect of reaction temperature on fold increase in fluorescence.
FIG. 4 is a standard operating curve for determining zinc ions.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention will be further described with reference to the following examples. It should be understood that the specific embodiments described herein are for purposes of illustration only and are not intended to limit the scope of the invention. On the contrary, the invention is intended to cover any alternatives, modifications, equivalents, and variations as may be included within the spirit and scope of the invention as defined by the appended claims. Further, in the following detailed description of the present invention, certain specific details are set forth in order to provide a thorough understanding of the present invention. The present invention will be fully understood by those skilled in the art without the details described herein.
The applicant experiment shows that each of the peripheral benzene rings has one nitro-substituted hollow phthalocyanine-tetranitro phthalocyanine capable of reacting with metal zinc ion in organic medium to produce obvious red fluorescent light with fluorescent intensity positively correlated with the amount of zinc ion. The invention establishes a novel zinc ion fluorescence quantitative analysis method by taking tetranitrophthalocyanine as a fluorescent probe. The invention has the advantages of strong specificity, high accuracy and sensitivity, simple and convenient operation and strong practicability.
The steps of the embodiment of the invention are as follows:
1) Adding an organic solvent as a reaction medium into a reaction vessel;
2) Adding the same volume of tetranitrophthalocyanine organic solution into each reaction container;
3) Sequentially adding zinc ion organic solution with increasing concentration;
4) Constant volume, mixing, preserving heat in water bath, transferring into ice water, and cooling;
5) Taking out the solution, scanning the fluorescence spectrum of the reaction system, and measuring the relative fluorescence intensity at the fluorescence peak.
Sequentially adding zinc ion organic solutions with increasing concentrations into a series of reaction containers, wherein the number of the reaction containers is not less than 3, and the series of zinc ion solutions is in the linear range of the corresponding working curve; by the linear range of the corresponding working curve is meant the range of the working curve corresponding to the determined concentration of zinc ions for the concentration of phthalocyanine solution used.
The phthalocyanine solution is added to a final concentration of 1.0X10 -6 ～2.0×10 -5 mol/L. After the volume of the reaction system is fixed, the reaction time is not less than 60min, and then the relative fluorescence intensity is measured in the wavelength range of 660-760 nm.
The molecular formula of the tetranitrophthalocyanine is as follows: c (C) 32 H 14 N 12 O 8 。
The structural formula is as follows:
the following is an example of experimental operation under optimized conditions.
45.0 μl of 1.5X10 concentration was added sequentially to a series of 5.0mL plastic centrifuge tubes -5 The concentration of 0.0, 3.0, 9.0, 15.0, 24.0, 30.0, 36.0, 45.0, 54.0, 60.0. Mu.L of the tetranitrophthalocyanine dimethylformamide solution in mol/L is 1.0X10 -4 The total volume of DMF solution of zinc ions, and dimethylformamide as the reaction medium was 3.0mL. Mixing, incubating in water bath at 60deg.C for 1.5 hr, transferring to ice water, cooling for 30min, taking out, recovering to room temperature, scanning emission spectrum on a fluorescence spectrophotometer, and measuring fluorescence intensity at 711nm.
The amounts of the components are shown in Table 1.
TABLE 1 amounts of the components of the reaction System
The present invention will be described in detail with reference to the drawings and tables.
1) Excitation spectrum and fluorescence spectrum of reaction system
FIG. 1 shows the excitation spectrum and fluorescence spectrum of a reaction system in the absence of zinc ions.
It is found that after zinc ions are added into the tetranitrophthalocyanine solution with extremely weak fluorescence, the system emits obvious red fluorescence, the fluorescence intensity is increased along with the increase of the concentration of the zinc ions, and a fluorescence peak appears at 711nm. In FIG. 1, the tetranitrophthalocyanine concentration is 1.5X10 -5 mol/L. The concentration of zinc ions is respectively: 0 (a, a'), 1×10 -7 (b,b′),3×10 -7 (c,c′),5×10 -7 (d,d′),8×10 -7 (e,e′),1×10 -6 (f,f′),1.3×10 -6 (g,g′),1.5×10 -6 (h,h′),1.8×10 -6 (i,i′)mol/L,2.0×10 -6 mol/L(j,j′)。
2) FIG. 2 is a comparison of the fluorescent response of tetranitrophthalocyanine to zinc ions and common metal ions.
Examination of tetranitrophthalocyanine as a common metal ion, namely Na + ，K + ，Mg 2+ ，Al 3+ ，Ba 2+ ，Mn 2+ ，Fe 2+ ，Fe 3+ ，Ni 2+ ，Co 2+ ，Cd 2+ ，Cu 2+ ，Hg + ，Hg 2+ ，Pb 2+ ，Zn 2+ Is a fluorescent response behavior of (1). The results show that tetranitrophthalocyanine has little fluorescence response to the metal ions, while in the presence of zinc ions, the fluorescence of the reaction system increases sharply, indicating that tetranitrophthalocyanine has a highly specific response to zinc ions. The concentration of all metal ions in FIG. 2 is 1.0X10 -6 mol/L。
3) FIG. 3 shows the effect of reaction temperature on the fluorescence enhancement factor
The change of the fluorescence enhancement factors of the reaction system at the temperature of 40, 50, 60, 70, 80, 100, 120 and 140 ℃ is examined, and the fact that the fluorescence enhancement factor of the reaction system at the temperature of 60 ℃ is the highest is found, so that the reaction is carried out under the condition of 60 ℃ in a water bath heating mode.
4) FIG. 4 is a standard operating curve for determining zinc ions.
Under the optimal condition, tetranitrophthalocyanine is taken as a fluorescent molecular probe, a standard working curve for measuring zinc ions is established, a linear regression equation of the curve is y=9.15x+5.40, r=0.9993, and the linear range of the method is 1.0x10 -7 ～2.0×10 -6 mol/L. The detection limit of the method is 3.0X10 -8 mol/L。
5) Table 2 is a table of the parameters for the reactions carried out in different solvents.
The reaction of zinc ions and tetranitrophthalocyanine in 47 different organic solvents is examined, and the fluorescence enhancement times of the reaction system are compared, so that the fluorescence enhancement times in n-amyl alcohol, DMF, ethanolamine, n-heptanol and isoamyl alcohol media are found to be larger. However, when the reaction is carried out in ethanolamine, the fluorescence intensity of the system is small, so that the relevant parameters when the reaction is carried out in n-pentanol, DMF, n-heptanol and isoamyl alcohol medium are examined in particular. The result of comprehensive analysis indicates that DMF is used as a reaction solvent, and the obtained standard working curve has wider linear range and better linearity.
TABLE 2
6) Table 3 shows the measurement results of the actual samples.
The invention is applied to the determination of the zinc oxide ointment of the actual sample. The zinc oxide ointment contains auxiliary materials such as vaseline and the like besides the main drug zinc oxide, and the zinc oxide cannot be directly dissolved in the solvent DMF used in the invention, so that the sample needs to be pretreated.
TABLE 3 Table 3
The specific treatment method comprises the following steps: accurately weighing 0.1000g of zinc oxide ointment into a 10mL centrifuge tube, adding 3mL of chloroform, fully dissolving in a water bath at 60 ℃, and centrifuging at 5000r/min for 5min after no suspended substances exist. The supernatant was discarded, and the precipitate was sufficiently dissolved with 1mol/L hydrochloric acid. The solution was transferred to a beaker and heated at 200 ℃ to volatilize the hydrochloric acid clean and give a solid. And (3) dissolving the solid by using DMF (dimethyl formamide) to a volume of 10.0mL, sucking 100 mu L and diluting to 10.0mL to obtain the solution to be tested.
Accurately sucking 30.0 mu L of the pretreated solution to be detected, detecting according to the established method steps, calculating the concentration of zinc ions according to the detected fluorescence intensity, further calculating the content of zinc oxide, comparing with the content of the sample mark, and ensuring satisfactory accuracy and reproducibility of the result.
The principle of the invention is that tetranitrophthalocyanine can react with zinc ions in an organic medium to generate a red fluorescent compound, the fluorescence intensity is in direct proportion to the concentration of the zinc ions, and the detection sensitivity is high and the specificity is strong. Adding an organic solvent, tetranitrophthalocyanine and zinc ion organic solution into a reaction container, fixing the volume, uniformly mixing, carrying out water bath heat preservation for a certain time, transferring into ice water for cooling, taking out, and scanning an emission spectrum or measuring the fluorescence intensity at a fluorescence peak. The measurement method established by the invention has strong specificity, excellent linear response and high sensitivity and accuracy; the wavelength of the measurement is in the red light region, the advantages of the long-wave fluorescent probe are fully exerted, the photobleaching effect of the measurement system is small, and the interference of sample background fluorescence and scattered light can be effectively eliminated.
The above-described embodiments are merely preferred embodiments of the present invention and should not be construed as limiting the scope of the present invention. All equivalent changes and modifications within the scope of the present invention are intended to be covered by the present invention.

Claims (7)

1. A fluorescence detection method for determining zinc ions by taking tetranitrophthalocyanine as a reagent is characterized by comprising the following specific steps:
1) Adding an organic solvent serving as a reaction medium into a reaction container, wherein the added organic solvent is one of N, N-dimethylformamide, N-amyl alcohol, isoamyl alcohol, N-heptanol, N-octanol and ethanolamine;
2) Adding the same volume of tetranitrophthalocyanine organic solution into each reaction container;
3) Sequentially adding zinc ion organic solution with increasing concentration;
4) Constant volume, mixing, preserving heat in water bath for a certain time, transferring into ice water, and cooling; the temperature of the heat preservation is 40-140 ℃, and the time of the water bath heat preservation is not less than 60min;
5) Taking out the solution, scanning the fluorescence spectrum of the reaction system, and measuring the relative fluorescence intensity at the fluorescence peak.
2. A fluorescence detection method for detecting zinc ions by using tetranitrophthalocyanine as a reagent according to claim 1, wherein in step 1), the number of the reaction vessels is not less than 3.
3. A fluorescent assay for determining zinc ions using tetranitrophthalocyanine as reagent as claimed in claim 1, wherein in step 2) the tetranitrophthalocyanine has the formula C 32 H 14 N 12 O 8 ；
The structural formula is as follows:
，
the organic solvent used in the tetranitrophthalocyanine organic solution is an organic solvent with relatively high solubility for tetranitrophthalocyanine, and is selected from N, N-dimethylformamide, dimethyl sulfoxide, chloronaphthalene, quinoline and nitrobenzene.
4. A fluorescent assay for determining zinc ions using tetranitrophthalocyanine as a reagent as claimed in claim 1, wherein in step 2), the tetranitrophthalocyanine solution is present at a final concentration of 1.0X10 -6 ~2.0 × 10 -5 A corresponding amount of tetranitrophthalocyanine solution in mol/L.
5. A fluorescence detection method for determining zinc ions using tetranitrophthalocyanine as a reagent according to claim 1, wherein in step 3), the solvent used in the zinc ion organic solution is an organic solvent having a high solubility for zinc compounds, selected from the group consisting of methanol, ethanol, propanol, acetone, acetonitrile, dimethylformamide, dimethylsulfoxide, sulfolane.
6. A fluorescence detection method for determining zinc ions using tetranitrophthalocyanine as a reagent according to claim 1, wherein in step 3), the series of concentrations of the zinc ion organic solution falls within a corresponding linear range of operating curves, which corresponds to the linear range of operating curves for determining the concentration of zinc ions determined by the concentration of the tetranitrophthalocyanine solution used.
7. A fluorescence detection method for detecting zinc ions according to claim 1, wherein in step 5), the relative fluorescence intensity at the peak of the measured fluorescence is measured in a wavelength range of 660 to 760 nm.
CN202111437993.5A 2021-11-30 2021-11-30 Fluorescent detection method for measuring zinc ions by taking tetranitrophthalocyanine as reagent Active CN114113018B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN202111437993.5A CN114113018B (en) 2021-11-30 2021-11-30 Fluorescent detection method for measuring zinc ions by taking tetranitrophthalocyanine as reagent

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN202111437993.5A CN114113018B (en) 2021-11-30 2021-11-30 Fluorescent detection method for measuring zinc ions by taking tetranitrophthalocyanine as reagent

Publications (2)

Publication Number Publication Date
CN114113018A CN114113018A (en) 2022-03-01
CN114113018B true CN114113018B (en) 2023-10-24

Family

ID=80367779

Family Applications (1)

Application Number Title Priority Date Filing Date
CN202111437993.5A Active CN114113018B (en) 2021-11-30 2021-11-30 Fluorescent detection method for measuring zinc ions by taking tetranitrophthalocyanine as reagent

Country Status (1)

Country Link
CN (1) CN114113018B (en)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104880444A (en) * 2015-05-21 2015-09-02 桂林理工大学 Method for determining kanamycin sulfate
CN108051412A (en) * 2017-11-27 2018-05-18 湖北师范大学 A kind of method of tetranitro aluminium phthalocyanine near-infrared fluorescent detection ascorbic acid
WO2021170781A1 (en) * 2020-02-28 2021-09-02 Technische Universität Berlin Fluorescent probes for detection of calcifications

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20070102635A1 (en) * 2005-11-08 2007-05-10 Zeying Ma Methods and systems for identifying ink

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104880444A (en) * 2015-05-21 2015-09-02 桂林理工大学 Method for determining kanamycin sulfate
CN108051412A (en) * 2017-11-27 2018-05-18 湖北师范大学 A kind of method of tetranitro aluminium phthalocyanine near-infrared fluorescent detection ascorbic acid
WO2021170781A1 (en) * 2020-02-28 2021-09-02 Technische Universität Berlin Fluorescent probes for detection of calcifications

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
叶飞.金属酞菁及衍生物的合成及性质研究.《中国优秀硕士学位论文全文数据库 (工程科技Ⅰ辑)》.2016,(第第12期期),全文. *
尹彦冰,郝向荣,李银艳,赵宝中,付强.2,9,16,23-四硝基酞菁钴(Ⅱ)的合成及光谱性质.东北师大学报(自然科学版).2004,(第01期),全文. *

Also Published As

Publication number Publication date
CN114113018A (en) 2022-03-01

Similar Documents

Publication Publication Date Title
Jiang et al. An ultra-sensitive and ratiometric fluorescent probe based on the DTBET process for Hg 2+ detection and imaging applications
CN108129459B (en) Novel fluorescent probe for detecting sulfur dioxide and application thereof
CN108083256A (en) The preparation method of high fluorescence property fluorescent carbon quantum dot and its in Cr（VI）Application in detection
CN108003869B (en) Fluorescent probe for detecting hypochlorite with high sensitivity and synthesis method and application thereof
Guo et al. An “OFF–ON” fluorescent chemosensor for highly selective and sensitive detection of Al (III) in aqueous solution
CN110229147A (en) A kind of cumarin-benzothiazolyl hydrazone compounds and its preparation method and application
Liu et al. Sensitive fluorescence assay for the detection of glyphosate with NACCu2+ complex
CN114136943B (en) Fluorescent analysis method for measuring lithium ions by taking empty phthalocyanine as molecular probe
Sun et al. Highly sensitive fluorescent sensor for copper (II) based on amplified fluorescence quenching of a water-soluble NIR emitting conjugated polymer
Pei et al. Dual colorimetric and near-infrared fluorescence probe for Hg2+ detection and cell imaging
Oguz et al. A basket-type fluorescent sensor based calix [4] azacrown ether for multi-analytes: Practicability in living cells and real sample
CN114516836A (en) Fluorescent probe material, preparation method thereof and method for detecting sulfide
CN112630279B (en) Gold nanoparticle-based plasma resonance enhanced electrochemical luminescence sensor for detecting dichlorophenolic acid and preparation method thereof
CN114113018B (en) Fluorescent detection method for measuring zinc ions by taking tetranitrophthalocyanine as reagent
CN106397319A (en) Fluorescent probe for proportionally detecting hydrazine, method for synthesizing fluorescent probe and application thereof
CN110878085B (en) Rapid high-selectivity hypobromous acid fluorescent probe, preparation method and application
CN115029132B (en) Preparation method of novel dopamine functional fluorescent carbon dots, product and application thereof
CN109053711B (en) Probe compound for mercury ion detection and preparation method and application thereof
CN1763020A (en) 3,3',5,5'-tetramethyl benzidine derivative and its preparation method and uses
CN114835636A (en) Naphthalene-vinyl pyridyl double-response type fluorescent probe and preparation method and application thereof
Peng et al. ESIPT-based fluorescent enhanced probes prompted by methylated β-cyclodextrin for the detection of thiophenols
CN112225743B (en) Quinolinyl near-infrared rhodamine fluorescent dye, ratiometric fluorescent probe, and synthesis and application thereof
CN109734647B (en) Fluorescent probe for detecting cysteine, and preparation method and use method thereof
CN108169196B (en) Method for rapidly detecting fluorine ions in environment
CN110698390B (en) Fluorescent probe for identifying bisulfite and preparation method and detection method thereof

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
GR01 Patent grant
GR01 Patent grant